WO2004027388A3 - Novel green and orange fluorescent labels and their uses - Google Patents

Novel green and orange fluorescent labels and their uses Download PDF

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Publication number
WO2004027388A3
WO2004027388A3 PCT/US2003/030167 US0330167W WO2004027388A3 WO 2004027388 A3 WO2004027388 A3 WO 2004027388A3 US 0330167 W US0330167 W US 0330167W WO 2004027388 A3 WO2004027388 A3 WO 2004027388A3
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WO
WIPO (PCT)
Prior art keywords
fluorescent
assays
compounds
labels
assay
Prior art date
Application number
PCT/US2003/030167
Other languages
French (fr)
Other versions
WO2004027388A2 (en
Inventor
Ram Bhatt
Michael J Conrad
Azzouz Bencheikh
Yifeng Xiong
Original Assignee
Chromagen Inc
Ram Bhatt
Michael J Conrad
Azzouz Bencheikh
Yifeng Xiong
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chromagen Inc, Ram Bhatt, Michael J Conrad, Azzouz Bencheikh, Yifeng Xiong filed Critical Chromagen Inc
Priority to AU2003272680A priority Critical patent/AU2003272680A1/en
Priority to EP03754878A priority patent/EP1546673A4/en
Publication of WO2004027388A2 publication Critical patent/WO2004027388A2/en
Publication of WO2004027388A3 publication Critical patent/WO2004027388A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/49—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C309/50—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/16—Isothiocyanates
    • C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
    • C07C331/20—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531—Production of immunochemical test materials
    • G01N33/532—Production of labelled immunochemicals
    • G01N33/533—Production of labelled immunochemicals with fluorescent label
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50—Pyrenes; Hydrogenated pyrenes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S436/00—Chemistry: analytical and immunological testing
    • Y10S436/80—Fluorescent dyes, e.g. rhodamine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Urology & Nephrology (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Cell Biology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Biotechnology (AREA)
  • Analytical Chemistry (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

The present invention provides novel fluorescent compounds and covalent attachment chemistries which facilitate the use of these compounds as labels for ultrasensitive and quantitative fluorescent detection of low levels of biomolecules. In a preferred embodiment, the fluorescent labels of this invention are novel derivatives of the hydroxy-pyrene trisulphonic and disulphonic acids which may be used in any assay in which radioisotopes, colored dyes or other fluorescent molecules are currently used. Thus, for example, any assay using labeled antibodies, proteins, oligonucleotides or lipids, including fluorescent cell sorting, fluorescence microscopy (including dark-field microscopy), fluorescence polarization assays, ligand, receptor binding assays, receptor activation assays and diagnostic assays can benefit from use of the compounds disclosed herein.
PCT/US2003/030167 2002-09-23 2003-09-23 Novel green and orange fluorescent labels and their uses WO2004027388A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003272680A AU2003272680A1 (en) 2002-09-23 2003-09-23 Novel green and orange fluorescent labels and their uses
EP03754878A EP1546673A4 (en) 2002-09-23 2003-09-23 Novel green and orange fluorescent labels and their uses

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41302502P 2002-09-23 2002-09-23
US60/413,025 2002-09-23

Publications (2)

Publication Number Publication Date
WO2004027388A2 WO2004027388A2 (en) 2004-04-01
WO2004027388A3 true WO2004027388A3 (en) 2004-06-10

Family

ID=32030955

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/030167 WO2004027388A2 (en) 2002-09-23 2003-09-23 Novel green and orange fluorescent labels and their uses

Country Status (4)

Country Link
US (2) US7317111B2 (en)
EP (1) EP1546673A4 (en)
AU (1) AU2003272680A1 (en)
WO (1) WO2004027388A2 (en)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7470420B2 (en) 2000-12-05 2008-12-30 The Regents Of The University Of California Optical determination of glucose utilizing boronic acid adducts
AU2003272680A1 (en) * 2002-09-23 2004-04-08 Chromagen, Inc. Novel green and orange fluorescent labels and their uses
CA2677009A1 (en) 2007-02-06 2008-08-14 Glumetrics, Inc. Optical systems and methods for rationmetric measurement of blood glucose concentration
US7751863B2 (en) 2007-02-06 2010-07-06 Glumetrics, Inc. Optical determination of ph and glucose
JP2010527010A (en) * 2007-05-10 2010-08-05 グルメトリクス、 インク． Apparatus and method for calibrating an analyte sensor
EP2162057A1 (en) 2007-05-10 2010-03-17 Glumetrics, Inc. Equilibrium non-consuming fluorescence sensor for real time intravascular glucose measurement
WO2009021057A1 (en) * 2007-08-06 2009-02-12 Glumetrics, Inc. Hpts-mono and bis cys-ma polymerizable fluorescent dyes for use in analyte sensors
WO2009067626A1 (en) 2007-11-21 2009-05-28 Glumetrics, Inc. Use of an equilibrium intravascular sensor to achieve tight glycemic control
EP2223086B2 (en) * 2007-12-14 2016-06-01 Biotium Inc. Fluorescent compounds - labeling dyes
DK2252584T3 (en) 2008-02-04 2017-01-16 Prozyme Inc COMPOUNDS AND PROCEDURES FOR QUICK LABELING OF N-GLYCANS
CU23844B1 (en) * 2009-04-17 2012-10-15 Ct De Neurociencias De Cuba PROCEDURE FOR OBTAINING NEW DERIVATIVES OF NAFTALENE FOR THE LIVE DIAGNOSIS OF ALZHEIMER'S DISEASE
US20120100997A1 (en) 2009-04-24 2012-04-26 University Of Southern California Cd133 polymorphisms and expression predict clinical outcome in patients with cancer
US20110077477A1 (en) * 2009-09-30 2011-03-31 Glumetrics, Inc. Sensors with thromboresistant coating
US8658434B2 (en) * 2009-10-28 2014-02-25 Biotium, Inc. Fluorescent pyrene compounds
US8467843B2 (en) 2009-11-04 2013-06-18 Glumetrics, Inc. Optical sensor configuration for ratiometric correction of blood glucose measurement
WO2011084757A1 (en) 2009-12-21 2011-07-14 University Of Southern California Germline polymorphisms in the sparc gene associated with clinical outcome in gastric cancer
WO2011085334A1 (en) 2010-01-11 2011-07-14 University Of Southern California Cd44 polymorphisms predict clinical outcome in patients with gastric cancer
EP2609426B1 (en) 2010-08-27 2018-12-19 The Texas A&M University System Fluorescence labeling reagents and uses thereof
DE102011101207B3 (en) * 2011-05-11 2012-05-10 Sartorius Stedim Biotech Gmbh Fluorescent dye for pH sensor
EP2769226B1 (en) 2011-07-15 2017-05-24 Medtronic Minimed, Inc. Combinations of fluorphores and pyridinium boronic acid quenchers for use in analyte sensors
US10436790B2 (en) 2011-09-28 2019-10-08 Waters Technologies Corporation Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals
US11352325B2 (en) 2011-09-28 2022-06-07 Waters Technologies Corporation Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals
WO2013049622A1 (en) 2011-09-28 2013-04-04 Waters Technologies Corporation Rapid fluorescence tagging of glycans and other biomolecules with enhanced ms signals
US20150329505A1 (en) * 2012-01-31 2015-11-19 Bioconst Pty Ltd A fluorescent composition for use in marking objects, such as flowers
DK3213056T3 (en) 2014-10-30 2020-09-28 Waters Technologies Corp PROCEDURES FOR QUICK PREPARATION OF LABELED GLYCOSYLAMINES AND FOR ANALYSIS OF GLYCOSYLED BIOMOLECULES WHICH PROVIDE THE SAME BACKGROUND
EP3218352B1 (en) 2014-11-13 2020-08-05 Waters Technologies Corporation Method for liquid chromatography calibration for labeled n-glycans, method for preparing a dextran ladder calibrant and calibrant
EP4234062A3 (en) 2016-06-21 2023-10-25 Waters Technologies Corporation Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties
CN109641846A (en) 2016-06-21 2019-04-16 沃特世科技公司 Pass through the glycan of the reduction amination of the MS signal for enhancing and the fluorescent marker of other biological molecule
EP3479103B1 (en) 2016-07-01 2022-04-20 Waters Technologies Corporation Methods for the rapid preparation of labeled glycosylamines from complex matrices using molecular weight cut off filtration and on-filter deglycosylation
CN107286038B (en) * 2017-07-03 2019-04-30 华南师范大学 (2- ethoxy) the pyrene formamide of N, N- bis- and its synthetic method and application
JP7113446B2 (en) * 2018-03-05 2022-08-05 国立大学法人東京工業大学 A no-wash protein gel stain based on pyrene
CN111073633B (en) * 2018-10-22 2023-07-25 北京工商大学 Naphthalene ring thiophenol fluorescent probe
JP7302847B2 (en) * 2019-04-23 2023-07-04 国立大学法人京都大学 Novel fluorodinitrophenyl compound and use thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1441021A (en) * 1973-01-05 1976-06-30 Ici Ltd Reactive pyrene dyestuffs
US5132432A (en) * 1989-09-22 1992-07-21 Molecular Probes, Inc. Chemically reactive pyrenyloxy sulfonic acid dyes

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT385755B (en) * 1986-06-13 1988-05-10 Koller Ernst METHOD FOR THE PRODUCTION OF NEW PYRENSULPHONIC ACID DERIVATIVES
JPH03502333A (en) * 1988-11-14 1991-05-30 ダウベン　ロバート　エム Fluorescent immunoassays and their fluorescent compounds and tracers
US5514710A (en) * 1994-01-11 1996-05-07 Molecular Probes, Inc. Photocleavable derivatives of hydroxyprenesulfonic acids
US5569366A (en) * 1995-01-27 1996-10-29 Beckman Instruments, Inc. Fluorescent labelled carbohydrates and their analysis
JP2002520448A (en) * 1998-07-10 2002-07-09 クロマジェン インコーポレーティッド New fluorogenic substrate for hydrolase
US6653141B2 (en) * 2000-12-05 2003-11-25 The Regents Of The University Of California Polyhydroxyl-substituted organic molecule sensing method and device
AU2003272680A1 (en) * 2002-09-23 2004-04-08 Chromagen, Inc. Novel green and orange fluorescent labels and their uses
WO2005064336A1 (en) * 2003-12-09 2005-07-14 Molecular Probes, Inc. Pyrenyloxysulfonic acid fluorescent agents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1441021A (en) * 1973-01-05 1976-06-30 Ici Ltd Reactive pyrene dyestuffs
US5132432A (en) * 1989-09-22 1992-07-21 Molecular Probes, Inc. Chemically reactive pyrenyloxy sulfonic acid dyes

Also Published As

Publication number Publication date
US7317111B2 (en) 2008-01-08
EP1546673A4 (en) 2006-08-09
AU2003272680A1 (en) 2004-04-08
EP1546673A2 (en) 2005-06-29
AU2003272680A8 (en) 2004-04-08
US7667048B2 (en) 2010-02-23
WO2004027388A2 (en) 2004-04-01
US20080261235A1 (en) 2008-10-23
US20040106806A1 (en) 2004-06-03

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